If this were anything like my high school math class, everyone else in the class would decide to copy my answer. In some cases, I have darn good reasons to believe I am significantly better than the average of the group I find myself in. For example, I give one of my freshman chemistry midterms. The test was multiple choice, with five possible answers for each question. My score was an 85 out of 100, among the highest in the class. The average was something like 42. On the final exam in that class, I had such confidence in my own answer that I declared that, for one of the questions, the correct answer was not among the responses offered—and I was right; one of the values in the problem was not what the professor intended it to be. I was also the only one in the class who had enough confidence to raise an objection to the question.
On the other hand, there are situations in which I would reasonably expect my estimate to be worse than average. If I wandered into the wrong classroom and had no idea what the professor was talking about, I’d definitely defer to the other students. If you ask me to predict the final score of a game between two well-known sports teams, I probably wouldn’t have heard of either of them and just choose something at random. (The average American can name the two teams playing in the Super Bowl when it occurs. I rarely can, and I don’t know whether to be proud or ashamed of this.) I also suspect that I routinely overestimate my chances of winning any given game of Magic. ;)
I’m not a random member of any group; I’m me, and I have a reasonable (if probably biased, given the current state of knowledge in psychology) grasp of my own relative standing within many groups.
Also, when you’re told that there is a hidden gotcha, sometimes you can find it if you start looking; this is also new information. Of course, you can often can pick apart any given hypothetical situation used to illustrate a point, but I don’t know if that matters.